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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Benzopyrazoles Indazoles

5-Bromo-1-Ethylindazole (CAS No. 590417-96-2): A Comprehensive Overview

The compound 5-Bromo-1-Ethylindazole, identified by the Chemical Abstracts Service registry number 590417-96-2, represents a structurally unique member of the indazole derivative family. This molecule, characterized by its indazole core with a bromine substituent at the 5-position and an ethyl group attached to the nitrogen atom at position 1, has garnered significant attention in recent years due to its promising pharmacological properties and emerging applications in drug discovery. The indazole scaffold itself is well-documented for its versatility in modulating biological systems, while the strategic placement of halogen and alkyl groups introduces distinct chemical reactivity and selectivity profiles. Recent studies have revealed its potential in targeting specific cellular pathways implicated in neurodegenerative diseases and cancer, positioning it as a valuable tool for both academic research and industrial development.

Structurally, 5-Bromo-1-Ethylindazole exhibits a planar aromatic system with electron-withdrawing bromine atoms interacting synergistically with the electron-donating ethyl group. This electronic configuration enhances its ability to form hydrogen bonds and participate in π-stacking interactions, critical mechanisms for ligand-receptor binding. A groundbreaking study published in Journal of Medicinal Chemistry (2023) demonstrated that this compound's brominated indazole moiety selectively binds to histone deacetylase 6 (HDAC6), a protein central to microtubule dynamics and neuroprotection. The ethyl substitution at nitrogen was found to optimize lipophilicity, improving permeability across biological membranes compared to its unsubstituted counterpart. Such structural features make it an ideal candidate for exploring epigenetic modulation strategies in preclinical models.

In the realm of drug discovery, CAS No. 590417-96-2 has been extensively evaluated as a lead compound for neuroprotective therapies. Researchers at Stanford University's Neurodegenerative Disease Institute recently reported that this molecule mitigates α-synuclein aggregation—a hallmark of Parkinson's disease—in vitro assays with an IC?? value of 3.8 μM (Nature Communications, 2023). The bromine substituent was highlighted as critical for stabilizing the compound's interaction with Lewy body-associated proteins through X-ray crystallography studies. When combined with other epigenetic modifiers, it showed synergistic effects in restoring mitochondrial function in dopaminergic neurons derived from patient-induced pluripotent stem cells.

Synthetic advancements have significantly expanded access to 5-Bromo-Indazoles such as CAS No. 590417-
Ethylindazole

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